Potassium Phosphate, Tribasic → HCID 117841056, compound

HRID 714884Notes

Reaction equation

HRID 714884 reaction equation
Br[C:2]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH:18]1(B(O)O)[CH2:20][CH2:19]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1.O>[CH:18]1([C:2]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:3]=2[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 68885345HCID 68885345, compound

Product 1

HCID 117841056HCID 117841056, compoundYield 99.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 22272177Toluene waterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl 2-bromo-4-nitrobenzoate (1.5 g) obtained in Step A of Example 301 in a mixed solvent of toluene-water (v/v=5/1, 18 mL) were successively added cyclopropylboronic acid (1.3 g), tripotassium phosphate (4.7 g), tricyclohexyl phosphine (280 mg) and palladium acetate (110 mg), and the mixture was stirred overnight at 100° C. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.3 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7cc2637e507a4f61ac6c15a3ee433d87
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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